Trifluoroacetic acid → 5,6-Difluoro-2,3-dihydro-1H-isoindol-1-one

HRID 877232Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 877232
[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][C:10]=1[F:11])[C:7](=O)[NH:6][CH:5]2[OH:13].FC(F)(F)C(O)=O.C([SiH](CC)CC)C>ClCCl>[F:11][C:10]1[CH:9]=[C:8]2[C:4](=[CH:3][C:2]=1[F:1])[C:5](=[O:13])[NH:6][CH2:7]2

Komponenten

5

Edukt 3

HCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 581363585,6-Difluoro-3-hydroxy-2,3-dihydro-1H-isoindol-1-one

Produkt 1

HCID 213653915,6-Difluoro-2,3-dihydro-1H-isoindol-1-one

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

748 mg of 5,6-difluoro-3-hydroxy-2,3-dihydro-1H-isoindol-1-one (crude product, about 4.04 mmol) were initially charged in 50 ml of dichloromethane, 3.8 ml (48.5 mmol) of trifluoroacetic acid and 1.3 ml (8.08 mmol) of triethylsilane were added and the mixture was stirred overnight at RT. The reaction mixture was then concentrated, and the residue was dissolved in dichloromethane and washed with sodium bicarbonate solution. The crude product was purified by chromatography on silica gel (mobile phase cyclohexane/ethyl acetate 1:1 to 0:1). This gave 72 mg (10.6% of theory) of the target compound.

Aufarbeitung

  1. concentrationThe reaction mixture was then concentrated
  2. dissolutionthe residue was dissolved in dichloromethane
  3. washwashed with sodium bicarbonate solution
  4. customThe crude product was purified by chromatography on silica gel (mobile phase cyclohexane/ethyl acetate 1:1 to 0:1)

Quellen und Nachweise

ORD-Eintrag
ord-f0faaf2f2896460b90cb995aae3a7162
Quelldatensatz
uspto-grants-2015_03
Patentnummer
US08987256B2

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